tert-butyl N-(3-chloro-2-hydroxypropyl)carbamate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of the product of Step 2 (7.0 g, 21.3 mmol) in DMF (14 mL) is cooled at 0° C. and treated with (3-chloro-2-hydroxy-propyl)carbamic acid tert-butyl ester (5.6 g, 27 mmol) and then lithium tert-butoxide (51 mL of a 1.0 M solution in THF) dropwise over 15 min. The reaction mixture is stirred for 20 h at room temperature and then treated with 40 mL of satd. NH4Cl and 100 mL of H2O. The solution is extracted with two portions of dichloromethane and the combined organic phases washed with H2O, brine and dried (MgSO4), filtered and concentrated. The crude product is purified by column chromatography (0–50% ethyl acetate-hexanes) to provide the title compound as a foam. treated with 40 mL of satd The solution is extracted with two portions of dichloromethane the combined organic phases washed with H2O, brine dried (MgSO4) filtered concentrated The crude product is purified by column chromatography (0–50% ethyl acetate-hexanes)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of the product of Step 2 (7.0 g, 21.3 mmol) in DMF (14 mL) is cooled at 0° C. and treated with (3-chloro-2-hydroxy-propyl)carbamic acid tert-butyl ester (5.6 g, 27 mmol) and then lithium tert-butoxide (51 mL of a 1.0 M solution in THF) dropwise over 15 min. The reaction mixture is stirred for 20 h at room temperature and then treated with 40 mL of satd. NH4Cl and 100 mL of H2O. The solution is extracted with two portions of dichloromethane and the combined organic phases washed with H2O, brine and dried (MgSO4), filtered and concentrated. The crude product is purified by column chromatography (0–50% ethyl acetate-hexanes) to provide the title compound as a foam. treated with 40 mL of satd The solution is extracted with two portions of dichloromethane the combined organic phases washed with H2O, brine dried (MgSO4) filtered concentrated The crude product is purified by column chromatography (0–50% ethyl acetate-hexanes)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of the product of Step 2 (7.0 g, 21.3 mmol) in DMF (14 mL) is cooled at 0° C. and treated with (3-chloro-2-hydroxy-propyl)carbamic acid tert-butyl ester (5.6 g, 27 mmol) and then lithium tert-butoxide (51 mL of a 1.0 M solution in THF) dropwise over 15 min. The reaction mixture is stirred for 20 h at room temperature and then treated with 40 mL of satd. NH4Cl and 100 mL of H2O. The solution is extracted with two portions of dichloromethane and the combined organic phases washed with H2O, brine and dried (MgSO4), filtered and concentrated. The crude product is purified by column chromatography (0–50% ethyl acetate-hexanes) to provide the title compound as a foam. treated with 40 mL of satd The solution is extracted with two portions of dichloromethane the combined organic phases washed with H2O, brine dried (MgSO4) filtered concentrated The crude product is purified by column chromatography (0–50% ethyl acetate-hexanes)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of the product of Step 2 (7.0 g, 21.3 mmol) in DMF (14 mL) is cooled at. 0° C. and treated with (3-chloro-2-hydroxy-propyl)carbamic acid tert-butyl ester (5.6 g, 27 mmol) and then lithium tert-butoxide (51 mL of a 1.0 M solution in THF) dropwise over 15 min. The reaction mixture is stirred for 20 h at room temperature and then treated with 40 mL of satd. NH4Cl and 100 mL of H2O. The solution is extracted with two portions of dichloromethane and the combined organic phases washed with H2O, brine and dried (MgSO4), filtered and concentrated. The crude product is purified by column chromatography (0-50% ethyl acetate-hexanes) to provide the title compound as a foam. treated with 40 mL of satd The solution is extracted with two portions of dichloromethane the combined organic phases washed with H2O, brine dried (MgSO4) filtered concentrated The crude product is purified by column chromatography (0-50% ethyl acetate-hexanes)